First of all: this is not a replacement for EasyPrivacy&Co. but rather an addition. It is unavoidable that EasyPrivacy will fail to block a tracking server occasionally, having X-Do-Not-Track header in these cases would be nice (at least once the industry starts respecting it). IMHO this feature is not something that the user needs to switch on explicitly - by adding EasyPrivacy or a similar list the user already indicated that he wants his privacy to be protected. Consequently, X-Do-Not-Track header should be sent automatically if such a list is present.
I think that this is best achieved using a special filter. We can even allow specifying exceptions for particular sites where this header shouldn't be sent - in case somebody gets the idea of blocking users sending out this header (which is unfortunately something to be considered as long as Adblock Plus stays the only major product supporting this feature). A new filter option should be the easiest solution:
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*$image,~image,donottrack
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*$image,~image,donottrack,domain=~example.com
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@@|example.com^$image,~image,donottrack
Comments? Suggestions? Objections?